Abstract
The isolation and identification of (Z,E)-α-farnesene[(3Z, 6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene] (III) as the major component of the secretion from the metathoracic scent gland of the cotton seed bug,Oxycarenus hyalinipennis, is reported. The compound was identified by a combination of [1H] NMR, [13C] NMR, UV, and mass spectral data and by comparison with a synthetic sample, prepared by dehydration of (E)-nerolidol. (Z,E)-α-Farnesene (III) has been recorded previously in insects (ants and termites), but this is the first report of its occurrence in a member of the Heteroptera. (E)2-Octenyl acetate (XIII) and 2-octenal (XIV) were identified as minor components of the secretion. In addition, three minor monoterpenoid and two other sesquiterpenoid components were detected and tentatively identified.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Adu-Mensah, K., andKumar, R. 1977. Ecology ofOxycarenus species (Heteroptera: Lygaeidae) in southern Ghana.Biol. J. Linn. Soc. 9:349–377.
Anet, E.F.L.J. 1970. Synthesis of (E,Z)-α-, (Z,Z)-α-, and (Z)-β-farnesene.Aust. J. Chem. 23:2101–2108.
Ashlock, P.D., andLattin, J. D. 1963. Stridulatory mechanisms in the Lygaeidae, with a new American genus of Orsillinae (Hemiptera: Heteroptera).Ann. Entomol. Soc. Am. 56:693–703.
Attvgalle, A. B., andMorgan, E.D. 1982. Structures of homofarnesene and bishomofarnesene isomers fromMyrmica ants.J. Chem. Soc. Perkin Trans. 1:949–951.
Attygalle, A. B., Cammaerts, M. C., andMorgan, E. D. 1983. Dufour gland secretions ofMyrmica rugulosa andMyrmica schencki workers.J. Insect Physiol. 29:27–32.
Blum, M. S. 1981 Chemical Defenses of Arthropods. Academic Press, New York.
Bowden, B. F., Coll, J. C., de Silva, E. D., de Costa, M. S. L., Djura, P. J., Mahendran, M., andTapiolas, D. M. 1983. Studies of Australian soft corals. XXXI. Novel furanosesquiterpenes from several sinularian soft corals.Aust. J. Chem. 36:371–376.
Bowers, W. S., Nault, L. R., Webb, R. E., andDutky, S. R. 1972. Aphid alarm pheromone. Isolation, identification, synthesis.Science 177:1121–1122.
Bowers, W. S., Nishino, C., Montgomery, M. E., andNault, L. R. 1977. Structure-activity relationships of analogs of the aphid alarm pheromone, (E)-β-farnesene.J. Insect Physiol. 23:697–701.
Cammaerts, M. C., Evershed, R. P., andMorgan, E. D. 1981. Comparative study of the Dufour gland secretions of workers of four species ofMyrmica ants.J. Insect Physiol. 27:59–65.
Cavill, G. W. K., andWilliams, P. J. 1967. Constituents of Dufour's gland inMyrmicagulosa.J. Insect Physiol. 13:1097–1103.
Cavill, G. W. K., Williams, P. J., andWhitfield, F. B. 1967. α-Farnesene, Dufour's gland secretion in the antAphaenogaster longicaps (F. Sm).Tetrahedron Lett. 23:2201–2205.
Crombie, L., King, R. W., andWhiting, D. A. 1975. Carbon-13 magnetic resonance spectra. Synthetic presqualene esters, related cyclopropanes and isoprenoids.J. Chem. Soc. Perkin Trans. 1:913–915.
Edwards, L. J., Siddall, J. B., Dunham, L. L., Uden, P., andKislow, C. 1973.trans-β-Farnesene, alarm pheromone of the green peach aphid.,Myzus persicae (Sulzer).Nature 241:126–127.
Fernandes, A., Duffield, R. M., Wheeler, J. W., andLaberge, W. E. 1981. Chemistry of the Dufour's gland secretions of North American andrenid bees (Hymenoptera: Andrenidae).J. Chem. Ecol. 7:453–463.
Gibson, R. W., andPickett, J. A. 1983. Wild potato repels aphids by release of aphid alarm pheromone. Nature 302:608–609.
Honda, K. 1981. Larval osmeterial secretions of the swallowtails (Papilio).J. Chem. Ecol. 7:1089–1113.
Maschwitz, U. 1971. Wasserstoffperoxidals Antiseptikum bei einer Wasserwanze. Naturwissenschaften 58:572.
Morgan, E. D., andWadhams, L. G. 1972. Chemical constituents of Dufour's gland in the antMyrimica rubra.J. Insect Physiol. 18:1125–1135.
Morgan, E. D., Parry, K., andTyler, R. C. 1979. The chemical composition of the Dufour gland secretion of the antMyrmica scabrinodis.Insect Biochem. 9:117–121.
Naya, Y., Prestwich, G. D., andSpanton, S. G. 1982. Sesquiterpenes from termite soldiers. Structure of Amiteol, a new 5β, 7β, 10β-eudesmane fromAmitermes excellens.Tetrahedron Lett. 23:3047–3050.
Olagbemiro, T. O., andStaddon, B. W. 1983. Isoprenoids from metathoracic scent gland of the cotton seed bugOxycarenus hyalinipennis (Costa) (Heteroptera: Lygaeidae).J. Chem. Ecol. In press.
Oroshnik, W. 1956. The synthesis and configuration of neo-b vitamin A and neoretinene-b.J. Am. Chem. Soc. 78:2651–2652.
Pasteels, J. M., Gregoire, J.-C., andRowell-Rahier, M. 1983. The chemical ecology of defense in arthropods.Annu. Rev. Entomol. 28:263–289.
Pickett, J. A., andGriffiths, D. C. 1980. Composition of aphid alarm pheromones.J. Chem. Ecol. 6:349–360.
Schaefer, C. W., andPupedis, R. J. 1981. A stridulatory device in certain Alydinae (Hemiptera: Heteroptera: Alydidae).J. Kans. Entomol. Soc. 54:143–152.
Staddon, B. W. 1979. The scent glands of Heteroptera.Adv. Insect Physiol. 14:351–418.
Staddon, B. W., Everton, I. J.,andGames, D.E. 1979. Organ specificity and scent constitution in Corixidae (Heteroptera: Hydrocorisae).Comp. Biochem. Physiol. 62B:259–262.
Sutherland, O. R. W., andHutchins, R. F. N. 1973. Attraction of newly hatched codling moth larvae (Laspeyresia pomonella) to synthetic stereo-isomers of farnesene.J. Insect Physiol. 19:723–727.
Vander Meer, R. K., Williams, F. D., andLofquen, C. S. 1981. Hydrocarbon components of the trail pheromone of the red imported fire antSolenopsis invicta.Tetrahedron Lett. 22:1651–1654.
Wearing, C. H., andHutchins, R. F. N. 1973. α-Farnesene, a naturally-occurring oviposition stimulant for the codling moth,Laspeyresia pomenella.J. Insect Physiol. 19:1251–1256.
Wientjens, W. H. J. M., Lakwijk, A. C., andVan Der Marel, T. 1973. Alarm pheromones of grain aphids.Experientia 29:658–660.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Knight, D.W., Rossiter, M. & Staddon, B.W. (Z,E)-α-farnesene: Major component of secretion from metathoracic scent gland of cotton seed bug,Oxycarenus hyalinipennis (Costa) (Heteroptera; Lygaeidae). J Chem Ecol 10, 641–649 (1984). https://doi.org/10.1007/BF00994225
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00994225